Photo by Vincent Ramundo

Search Middletown Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Cottages in Middletown

Exterior
Hello Small Stone

Hello Small Stone

Middletown
9.6 out of 10, Exceptional, (5)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
United States
David
$369 nightly
The price is $417
Nov 13 - Nov 14
Total with taxes and fees
Hello Small Stone
Exterior
Cozy Haven: A Romantic Retreat in our Tiny House!

Cozy Haven: A Romantic Retreat in our Tiny House!

Middletown
7.0 out of 10, Good, (9)
"I love the place but the cleanliness was bad, we found a condom under the bed and there was also blood on the bed sheets and a yellow stain on the bed. I’m sorry but for the price I expected something better than this."
United States
Jeferson Eleazar P.
$208 nightly
The price is $246
Nov 11 - Nov 12
Total with taxes and fees
Cozy Haven: A Romantic Retreat in our Tiny House!
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen
9.8 out of 10, Exceptional, (11)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
United States
Teresa
$281 nightly
The price is $293
Nov 11 - Nov 12
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Bloomingburg
10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
$191 nightly
The price is $215
Nov 11 - Nov 12
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
House (1 Bedroom) | Interior
Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
Westbrookville
$271 nightly
The price is $306
Nov 12 - Nov 13
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
Exterior
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Sparrow Bush
9.4 out of 10, Exceptional, (11)
"Peaceful, comfortable, serene, just what we were looking for...felt like home."
United States
Blanche R.
$246 nightly
The price is $279
Nov 12 - Nov 13
Total with taxes and fees
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Terrace/patio
Cozy Cottage with Woodstock Scavenger Hunt

Cozy Cottage with Woodstock Scavenger Hunt

Mongaup Valley
10.0 out of 10, Exceptional, (6)
"Great little cottage close to Bethel Woods."
United States
Erin
$247 nightly
The price is $278
Nov 12 - Nov 13
Total with taxes and fees
Cozy Cottage with Woodstock Scavenger Hunt
Exterior
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Kerhonkson
9.4 out of 10, Exceptional, (12)
"The Dream Cottage at the Gunks is a perfect place for a cozy stay in a scenic location. Everything was very clean and decorated with good taste. Although we were not there much due to how much we did over the weekend, our time there was very pleasant. I highly recommend staying at this property."
United States
kim h.
$223 nightly
The price is $226
Dec 2 - Dec 3
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Outdoor dining
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
Vernon Township
8.8 out of 10, Excellent, (3)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Nov 11 - Nov 12
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (126)
"I cannot say enough on this location. Peaceful, and the view was extraordinary. Highly recommend this to anyone that wants a getaway."
United States
Daniel R.
$272 nightly
The price is $308
Nov 11 - Nov 12
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor dining
Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom

Highland Lake
10.0 out of 10, Exceptional, (33)
"Truly a great getaway from the city for relaxation and nature. A beautiful property with great amenities to make it feel like home. The host checked in often and was very responsive. Great place to bring kids and enjoy the outdoors even in the cold winter! "
United States
Anand S.
$787 nightly
The price is $851
Nov 17 - Nov 18
Total with taxes and fees
Lakefront | Sport Courts | HotTub | GameRoom
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"clean rooms "
christine 1-night trip
Posted 8 hours ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Middletown

Middletown Cottages information

Number of reviews
194
Accommodation
136 Cottages
Lowest Price
$215
Highest Price
$851

Frequently asked questions

Why book your cottage in Middletown with Expedia?
We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Middletown?
With Expedia's useful filter tool, sourcing cheap cottages in Middletown is a cinch. To discover accommodations that'll make your wallet smile, narrow down your search by budget, amenities and star rating.
What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.

Explore a world of travel with Expedia